Organic Chemistry Rxns

Front 1

Alkene + HX (hydrogen halide)

Back 1

Halogenation - follows Markovnikov's rule

Front 2

Alkene + Water w/ acid catalyst

Back 2

Alcohol - follows Markovnikov's rule

Front 3

Alkene + alcohol w/ acid catalyst

Back 3

Methoxy group added - follows Markovnikov's rule

Front 4

Alkene + Cl2 in CH2Cl2

Back 4

Cl adds to each C of double bond yielding halogenated alkane

Front 5

Alkene + Br2 in CH2Cl2

Back 5

Br adds to each C of double bond yielding halogenated alkane

Front 6

Alkene + Br2 in water

Back 6

Br adds Markovnikov (to C with most H's) and OH adds to other C of double bond

Front 7

Oxymercuration-reduction
Alkene +
1. HG(OAc)2, water, THF
2. NaBH4

Back 7

Alcohol - follows Markovnikov's rule

Front 8

Alkoymercuration-reduction
Alkene +
1. Hg(O2CCF3)2, CH3)H
2. NaBH4

Back 8

Methoxy group added - follows Markovnivkov's rule

Front 9

Alkene + peroxyacid

Back 9

Epoxide + carboxylic acid
Middle O of COOH forms epoxide

Front 10

Hydroboration-oxidation
Alkene +
1. BH3/THF
2. HO-, H2O2, water

Back 10

Alcohol - ANTI Markovnikov so OH adds to C with most H's

Front 11

Alkene + H2 with
Pd/C or Pt/C or Ni

Back 11

Reduction of double bond to produce alkane

Front 12

Alkyne + HX (hydrogen halide)

Back 12

1 eq - halogenation following Markovnikov's rule
excess - geminal dihalide formed following Markovnikov's rule

Front 13

Alkyne + Cl2 in CH2Cl2

Back 13

1 eq. - Cl adds to each C of triple bond and reduced to alkene
excess - two Cl's add to each C of triple bond and reduced to alkane

Front 14

Internal alkyne + water and acid
OR
Internal alkyne +
1. BH3/THF
2. HO-, H2O2, water

Back 14

Two ketones - carbonyl group on either of the C of the triple bond

Front 15

Terminal alkyne + H2O + acid + HgSO4

Back 15

Alcohol (Markovnikov) with double bond that tautomerizes to a ketone

Front 16

Terminal alkyne +
1. Disiamylborane
2. HO-, H2O2, water

Back 16

Alcohol (ANTI Markovnikov) ith double bond that that tautomerizes to aldehyde

Front 17

Alkyne + two H2 with
Pd/C or Pt/C or Ni

Back 17

Alkane

Front 18

Alkyne + H2 with Lindlar catalyst

Back 18

CIS Alkene

Front 19

Alkyne + H2 with Na or Li in NH3

Back 19

TRANS Alkene

Front 20

Terminal alkyne with
1. NaNH2
2. RCH2Br

Back 20

Removal of proton in first step followed by addition of CH2R

Front 21

Isolated diene + HBr (excess)

Back 21

Both double bonds of isolated diene will undergo electrophilic addition following Markovnikov's rule

Front 22

Isolated diene + 1 eq. HBr

Back 22

Only most reactive double bond of isolated diene will undergo electrophilic addition following Markovnikov's rule

Front 23

Conjugated diene + HBr

Back 23

Undergoes 1,2 and 1,4 addition in the presence of one equivalent of electrophilic reagent

Front 24

Diels-Alder Rxn
Conjugated diene + dienophile

Back 24

Cyclohexene with carbonyl and R group

Front 25

SN2 Characteristics

Back 25

One-step mechanism
No carbocation formation
Relative reactivities of alkyl halides CH3X > 1 > 2 > 3
Only inverted product formed

Front 26

SN1 Characteristics

Back 26

Two-step mechanism
Carbocation intermediate - rearrangement possible
Relative reactivities of alkyl halides 3 > 2 > 1 > CH3X
Both inverted and noninverted products are formed

Front 27

E2 Characterisitcs

Back 27

One-step mechanism
Relative reactivities of alkyl halides 3 > 2 > 1
Anti elimination - both E and Z stereoisomers formed (Isomer with bulkiest groups on opposite sides formed in greatest yields)

Front 28

E1 Characterisitics

Back 28

Two-step mechanism
Carbocation intermediate - rearrangement possible
Relative reactivities of alkyl halides 3 > 2 > 1
Anti and syn elimination - both E and Z stereoisomers formed (Isomer with bulkiest groups on opposite sides formed in greatest yield)

Front 29

Competing SN2 and E2 Reactions

Back 29

Primary alkyl halides - primarily substitution
Secondary alkyl halides - both
Tertiary alkyl halides - only elimination

Front 30

Competing SN1 and E1 Reactions

Back 30

Primary alkyl halides - cannot undergo either
Secondary alkyl halides - both
Tertiary alkyl halides - both

Front 31

Alcohol + HX (hydrogen halide) + heat

Back 31

Alkyl halide

Front 32

ROH + PBr3 with pyridine

Back 32

RBr

Front 33

ROH + PCl3 with pyridine

Back 33

RCl

Front 34

ROH + SOCl2 with pyridine

Back 34

RCl

Front 35

ROH + sulfonyl chloride

Back 35

Sulfonate ester + HCl